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Acid-Catalyzed Conversion and Self-Condensation

1. Refer to attached rxn. Write the complete stepwise mechanism for the acid-catalyzed conversion of the enol into its keto form, Compound C.

2. Give major organic products. Show all relevant stereochemistry.

3 and 4. Draw the structure of the aldol self-condensation product for each of the following compounds. If a compound does not undergo aldol self-condensation, explain why it does not.

5. In the alkylation of cyclohexanone, better yields are obtained by first reacting cyclohexanone with an equivalent of lithiumdiisopropylamide in THF and then adding the alkyl halide, rather than mixing cyclohexanone, alkyl halide, and a catalytic amount of sodium ethoxide in ethanol. Explain this observation by pointing out what the problems with the second reaction conditions might be and how the first set of reaction conditions help alleviate the problems.


Solution Preview

For questions 1-4, please see the attached file for the solutions.

5) When LDA (Lithium diisopropylamide) in THF is added to cyclohexanone and then alkyl bromide ...

Solution Summary

This solution provides guidelines for questions of organic chemistry on acid-catalyzed conversions, stereochemistry, self-condensation, and yields in reactions.